Fluopyram

Fluopyram	Last updated: 25/08/2024
(Also known as: AE C656948)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Persistent; GUS: High leachability	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health Moderate alert: Mammals chronic toxicity: Moderate; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A broad spectrum fungicide for use as a foliar application and as a seed treatment to control various diseases. Also has nematicide activity.

Example pests controlled

Botrytis, Powdery mildew, Fusarium virguliforme

Example applications

Potatoes; Sugarbeet; Fruit including apples, grapes and strawberries; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

2011, first registrations

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Denmark

Date EC 1107/2009 inclusion expires

31/06/2026

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓	✓	✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓		✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway
	✓

Additional information

Also used in

Iran, Australia, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₆H₁₁ClF₆N₂O

Canonical SMILES

C1=CC=C(C(=C1)C(=O)NCCC2=C(C=C(C=N2)C(F)(F)F)Cl)C(F)(F)F

Isomeric SMILES

International Chemical Identifier key (InChIKey)

KVDJTXBXMWJJEF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H11ClF6N2O/c17-12-7-9(15(18,19)20)8-25-13(12)5-6-24-14(26)10-3-1-2-4-11(10)16(21,22)23/h1-4,7-8H,5-6H2,(H,24,26)/f/h24H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Nematicide

Substance groups

Benzamide fungicide; Pyridine fungicide; Unclassified nematicide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Succinate Dehydrogenase Inhibitor.

CAS RN

658066-35-4

EC number

619-797-7

CIPAC number

807

US EPA chemical code

080302

PubChem CID

11158353

CLP index number

616-219-00-5

Molecular mass

396.76

PIN (Preferred Identification Name)

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide

IUPAC name

N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-α,α,α-trifluoro-ortho-toluamide

CAS name

N-(2-(3-chloro-5-(trifluoromethyl)-2-pyridinyl)ethyl)-2-(trifluoromethyl)benzamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Bayer CropScience
Nanjing Agrochemical Co., Ltd.

Example products using this active

Fluopyram SC 500
Verango
Velum
Propulse SE 250

Formulation and application details

Both seed treatments and suspension concentrate products for foliar application are available

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

16.0

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

250000

Acetone

250000

Dichloromethane

660

n-Heptane

62200

Toluene

Melting point (°C)

117.5

Boiling point (°C)

318

Degradation point (°C)

300

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

2.00 X 10⁰³

Calculated

Log P

3.3

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.2 X 10^-03

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

2.98 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

216nm=14877, 270nm=4332, 290nm<10

Surface tension (mN m⁻¹)

59.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

309

Persistent

DT₅₀ (lab at 20 °C)

309

Persistent

DT₅₀ (field)

118.8

Persistent

DT₉₀ (lab at 20 °C)

723

Very persistent

DT₉₀ (field)

833

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 117-717 days, DT₉₀ range 538->1000 days, Field studies DT₅₀ range 93.2-144.6 days, DT₉₀ range 487->1000 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.0

Note

Published literature RL₅₀ range 1.6-9.0 days, 5 crops grown in field & undercover, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable at pH 5, 7 & 9 at 50 °C

Water-sediment DT₅₀ (days)

1077

Stable

Water phase only DT₅₀ (days)

20.5

Slow

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

4.41

Moderately mobile

K_foc (mL g⁻¹)

278.9

¹/_n

0.827

Notes and range

EU dossier K_f range 2.94-6.83 mL g⁻¹, K_foc range 233-400 mL g⁻¹, ¹/_n range 0.765-0.948, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.23

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

4.46 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

20.78

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

3.4

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-hydroxyethyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10065)

Minor fraction

0.042

AE C656948-benzamide

Minor fraction

3-(methylsulfinyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: AE 1344122)

AE C656948-pyridyl-carboxylic acid

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)ethyl))-2-(trifluoromethyl)benzamide
Note: MWt=412.72

AE C656948-N-oxide

Plant

N-((E)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10627)
Note: MWt=394.71

AE C656948-N-olefine

Animal

N-((Z)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10650)
Note: MWt=394.71

AE C656948-Z-olefine

Animal

-
Note: MWt=586.83

AE C656948-enol-GA

Rat

-
Note: MWt=412.72

AE C656948-phenol

Animal

-
Note: MWt=574.87

AE C656948-phenol-glc

Rat

-
Note: MWt=588.85

AE C656948-phenol-GA

Animal; Rat

-
Note: MWt=412.72

AE C656948-benzamide

Animal; Rat; Plant

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanol
Note: MWt=225.60

AE C656948-pyridyl-hydroxyethyl

Animal

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl beta-D-glucopyranoside
Note: MWt=387.3

AE C656948-hydroxyethyl-glc

Plant

-
Note: MWt=549.89

AE C656948-hydroxyethyl-di-glc

Plant

-
Note: MWt=401.73

AE C656948-hydroxyethyl-GA

Animal; Rat

-
Note: MWt=241.6

AE C656948-ethyl-diol

Rat

-
Note: MWt=417.73

AE C656948-ethyl-diol-GA

Rat

-
Note: MWt=239.58

AE C656948-pyrodyl-acetic acid

Animal; Rat; Plant

-
Note: MWt=255.58

AE C656948-hydroxy-PAA

Animal; Rat

-
Note: MWt=401.73

AE C656948-PAA-glycoside

Plant

-
Note: MWt=356.75

AE C656948-pyridyl-methyl-cystein

Rat

Ref: BCS-AA10634
Note: MWt=360.26

AE C656948-lactame

Photolysis

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranosiduronic acid
Note: MWt=588.85

AE C656948-7-OH-GA

Animal; Fish; Rat

Ref: AE C657188
Note: MWt=225.26

AE C656948-pyridyl-carboxylic acid

Rat; Plant

3-(methylsulfinyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: AE 1344122)
Note: MWt=253.20

AE C656948-methyl-sulfoxide

Plant

3-chloro-2-methyl-5-(trifluoromethyl)pyridine
Note: MWt=195.57

AE C656948-picoline

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl 6-O-(carboxyacetyl)-beta-D-glucopyranoside
Note: MWt=660.91

AE C656948-8-hydroxy-glc-MA

Plant

-
Note: MWt=251.23

AE C656948-BA-methyl-sulfoxide

Rat

-
Note: MWt=267.23

AE C656948-BA-methyl-sulfone

Rat

-
Note: MWt=285.2

AE C656948-benzamide-SA

Rat

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)phenyl)carbonyl)amino)ethyl hydrogen sulfate
Note: MWt=492.78

AE C656948-7-OH-SA

Plant

N-(2-(3-chloro-5-(trifluoromethyl)pyridine-2-yl)-2-(beta-D-glucopyranosyloxyethyl)-2-(trifluoromethyl) benzamide
Note: MWt=574.87

AE C656948-7-hydroxy-glc

Plant

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranoside
Note: MWt=660.91

AE C656948-7-hydroxy-glc-MA

Plant

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl)-beta-D-glucopyranosiduronic acid
Note: MWt=588.85

AE C656948-8-OH-GA

Animal; Fish; Rat

-
Note: MWt=428.72

AE C656948-7-OH-phenol

Rat

-
Note: MWt=604.85

AE C656948-7-OH-phenol-GA

Rat

-
Note: MWt=508.78

AE C656948-7-OH-phenol-SA

Rat

-
Note: MWt=490.81

AE C656948-7-OH-methyl-sulfone

Rat

-
Note: MWt=524.78

AE C656948-7-OH-hydroxyphenol-SA

Rat

N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)-1-hydroxyethyl)-2-(trifluoromethyl)benzamide
Note: MWt=412.72

AE C656948-8-hydroxy

Animal; Fish; Rat; Plant

1-O-((2-trifluoromethyl)benzoyl)amine)-beta-D-glucopyranuronic acid
Note: MWt=365.3

AE C656948-benzamide-N,O-GA

Rat

2-(trifluoromethyl)benzoic acid
Note: MWt=190.12

AE C656948-benzoic acid

Rat; Plant

-
Note: MWt=604.85

AE C656948-di-8-OH-GA

Animal; Rat

-
Note: MWt=766.99

AE C656948-hydroxy-glyc-gluc

Plant

-
Note: MWt=634.87

AE C656948-methoxy-di-OH-GA

Rat

N-acetyl-O-(2-(trifluoromethyl)benzoyl)serine
Note: MWt=319.24

AE C656948-benzoyl-serine

Rat

-
Note: MWt=205.14

AE C656948-hydroxy-benzamide

Rat

-
Note: MWt=381.2

AE C656948-benzamide-OH-GA

Rat

-
Note: MWt=350.32

AE C656948-benzamide-cysteine

Rat

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 82.8

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1643 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

4.5

Colinus virginianus NOAEL

High

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

11.42

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effects
Carbon mineralisation: No significant adverse effect

Dose: 3.33 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

103.8

Folsomia candida

Non-target plants

> 0.25

Fagopyrum esculentum
Seedling emergence, ER₅₀
as g ha⁻¹

> 0.50

Beta vulgais
Vegetative vigour, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 102.3

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 2000

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 2000

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.98

Coleonyx variegatus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.135

Pimephales promelas 33 day

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 100

Daphnia magna

Low

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

1.25

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

1.39

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

2.32

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 1.13

Skeletonema costatum

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.11

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.012

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.5

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.05

Rat SF=100

Dermal penetration studies (%)

1-3

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for intended uses

Occupational

Acceptable for intended uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Extensively metabolised and excreted within 7 days via the urine and faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, thyroid and blood toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H411

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

fluopyram

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

fluopyram

Hungarian

Dutch

Norwegian

fluopyram

Record last updated:	25/08/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242